Michael K. Williams Has a Story You Need to Read to Believe

Michael K. Williams—best known for playing complicated badasses on The Wire and Boardwalk Empire—spent the winter of 2015 commuting from Williamsburg to Yonkers, where HBO had built a Rikers Island prison set for its haunting seven-part drama The Night Of. But it wasn’t the gray trip in bitter nor’easter weather that snapped Williams into character as Freddy, a powerful prisoner who takes a young inmate (played by Riz Ahmed) under his wing. It was the fact that Williams had driven this heart-wrenching route many times before, on his way to Green Haven Correctional Facility—the maximum-security prison farther north. That’s where the actor’s nephew, Dominic Dupont, is currently incarcerated, nearly 20 years after his conviction for murder.

“It was surreal,” Williams tells Vanity Fair of the eerily evocative journey. And each day of filming concluded with another emotional trigger. The actor would exit his character’s cement cell block and walk free—something his nephew has not done for nearly two decades.

“I’ve long made peace with who my nephew is,” Williams says. “When he first got arrested I couldn’t leave the prison without crying.” Now, though, he realizes that his nephew’s presence is a blessing for “the young men that he’s mentoring in there. I’ve come to realize that these men would have never had the access to him had he not been there.”

Williams has always made his performances deeply personal, returning to the darkness he experienced growing up in the public housing projects of East Flatbush, Brooklyn. Though agonizing, those memories are filled with textures he summons to elevate his characters beyond what is written, making The Wire’s Omar Little and Boardwalk Empire’s Chalky White beloved and memorable years after their final scenes.

Incredulously, Williams did not earn a single Emmy nomination during the 10 total seasons those HBO dramas aired. This time around, for The Night Of, Williams happened to earn a nomination. But that wasn’t the motivation for hurtling himself down another painful rabbit hole to find Freddy.

“After I left The Wire, I realized how important it was to play characters that are in such pain,” he explains. Furthermore, in a culture inundated with criminal-justice franchises and their tidy television conclusions, it was important for Williams to take part in something that realistically depicted the judicial system he had seen swallow so many friends and family members.

Courtesy of HBO.

“I knew that [creators Richard Price and Steven Zaillian] weren’t trying to sensationalize the prison experience,” Williams says. “They wanted to show what really happens when you get arrested in New York City. It’s really fucking long and dark. You don’t get to see the judge because the episodic hour is over. You’re sitting and waiting to see your lawyer, waiting to see the judge, waiting to be arraigned, waiting to get sentenced, waiting to see the parole board. All you have in jail is time. The question becomes, what do you do with that time.”

Williams has built a career finding unexpected nuance in tough-guy roles. But growing up in Brooklyn, Williams was actually ridiculed for his inability to summon the machismo he would later channel effortlessly onscreen.

“From some of the characters I play now, you’d probably think I was about The Godfather [growing up],” Williams says. “But the movies that inspired me early on were weird—like Saturday Night Fever,Purple Rain, and Grease. I like musicals.”

In that case, it makes sense that Williams’s artistic awakening came courtesy of Janet Jackson.

In 1989, while in his early 20s, Williams had seemingly righted his career path. He had gotten the drug addiction that derailed his teens under control, and had a stable job managing blueprints for Pfizer Pharmaceuticals. Then he saw the music video for Jackson’s “Rhythm Nation.”

“My spirit was stirred by the visual images that were shown . . . different people, some tall, some short, male, female, light-skinned, dark-skinned,” Williams told NPR last year. “It wasn’t just everybody was pretty with perfect teeth. You saw some jagged edges . . . and when they all came together, they moved like one.”

“The message of the song—about getting rid of color lines, not judging—I just identified with it across the board, and I was like, ‘I want to become a Janet Jackson background dancer,’” Williams has said. “‘I think she will understand me.’”

Williams quit his job managing someone else’s blueprints, and started drawing his own. He fired up his VHS player, recorded all of Jackson’s music videos, and watched them until he learned how to count steps. He calls himself “a hack,” but he mined a seven-year career dancing in music videos and on tours for Madonna,Missy Elliott,Crystal Waters, and Ginuwine.

The informal education did have one early drawback: “A friend of mine challenged me to a Janet Jackson dance competition, and I made a complete ass out of myself because up until that moment I’d watch her, and I’d go the exact same way with her as the television,” he laughs. “When you’re dancing with her, you’ve got to go the opposite of the fucking TV.”

After spending his early years mocked for not fitting the alpha-male archetype, the public’s perception of Williams literally changed overnight in 1991. The night before turning 25, he got into a bar fight in Queens, and a stranger dragged a razor blade down his face and across his jugular.

“Things changed immediately after that,” Williams has said. “Directors didn’t want me just to dance in the videos any more. They wanted me to act out these thug roles, you know, like, ‘Mike, roll these—roll these dice in this video. Have this fight in this video.’”

Until that point, Williams had never considered acting a viable career option. But the early 90s influx of gritty dramas like Boyz n the Hood,Juice,Menace II Society,Dead Presidents, and Above the Rim resonated with Williams, reflecting the very struggles of masculine identity and inner-city life he experienced growing up.

“Those movies were planting seeds in my head that I didn’t know yet. . . They were showing me that I could do it.”

Another unbelievable twist of fate struck several years later: while casting the 1996 crime-drama Bullet, Tupac Shakur noticed a Polaroid picture of Williams from a music-video audition that happened to be hanging in a New York City production office. Williams thinks that Shakur must have recognized the pain in his eyes and the courage it took to get in front of a camera, with that scar running down his face like some violent metaphor; Shakur ended up tapping Williams to play his brother.

Six years later, Williams won his breakout part as Omar on The Wire. The show’s co-creator Ed Burnshas said that the scar earned him the spot on the Peabody-winning drama. But it was Williams’s talent and fearlessness that made Omar a complex, zeitgeist-capturing antihero.

The fascinating character—a gay stick-up man navigating Baltimore’s drug-infested inner streets with a strict moral code, a sawed-off shotgun, and a clean vocabulary—was a pop-culture hit. And after filming the first season, Williams found that he was suddenly being celebrated on the same Brooklyn streets where he had been bullied decades earlier.

The newfound respect was alluring, but confusing. For decades, the actor—who has spoken openly about his struggles with addiction—had been in pain. But those internal wounds didn’t pay off in street credibility. When the line between Omar and Michael began to blur off-screen—with strangers saluting Williams as Omar—he suffered a sort of identity crisis, backsliding into drug addiction and burning through his paychecks.

Williams has credited Barack Obama with pulling him out of his downward spiral in the spring of 2008, after The Wire ended. In the middle of a three-day cocaine bender, Williams accompanied his mother to a rally for the future president in Harrisburg, Pennsylvania. By then, Obama had publicly declared Omar his favorite character on the series. According to The New York Times, “when the two men met privately after the event, Mr. Williams, lock-jawed and high on cocaine, could barely speak.”

“Hearing my name come out of his mouth woke me up,” he told the Times. “I realized that my work could actually make a difference.”

Since that moment, Williams has been just as brave in his work but with a new support system in place.

“When you go into characters like that, you’ve got to put a little lasso around your ankle and then tell your friends to hold the other side of the rope and pull you out if it gets too deep,” Williams says now. “They were that for me on The Night Of. You keep a good team around you when you tell stories like that, because they’re heavy. They’re dark.”

Nearly 10 years after that eye-opening Obama encounter, Williams chooses roles with purpose—like real-life gay activist Ken Jones in ABC’s historical drama When We Rise and a Vietnam veteran in SundanceTV’s Hap and Leonard.

He is an A.C.L.U. ambassador for ending mass incarceration, and recently finished a documentary about the criminal justice system (tentatively titled Diamond in the Rough), which will air on HBO through Vice. The film shadows the struggles of his nephew, Dominic, and his Wire co-star Felicia Pearson.

This past spring, he starred in a short about typecasting for The Atlantic that is more thought-provoking than most full-length studio films. In it, Williams plays various versions of himself, toying with the question that faces many minority actors working in Hollywood: has he been typecast? He’s played a variety of criminals in his career, and one early character, in Martin Scorsese’s 1999 drama Bringing Out the Dead, was simply named Drug Dealer.

“Look, I picked these roles,” Williams tells another version of himself, who called him out for having played “gangster Mike, old-timey gangster Mike, Southern gangster Mike.”

“I made this path for myself.”

“Did you? Or did they choose you? You think we would have been doing what we doing if we had a choice?”

“If I were typecast I would be in jail or dead,” Williams tells himself. “But I’m here. I got myself out.”

Indeed, this past March, Williams reached the Hollywood holy grail when he was invited to join the Star Wars franchise for the Han Solo spin-off.

“I was surprised I got the project in the first place,” Williams confesses. “I fanned out a little bit when Chewbacca walked on set. I kind of freaked out and hugged him at the waist. All you can grab is the waist because he’s so tall.”

Williams had already filmed all of his scenes as a new character to the universe—“a link between Han Solo and Emilia’s character, Kira”—when Lucasfilm suddenly announced in June that it was replacing directors Phil Lord and Chris Miller with Ron Howard. The shake-up meant that Williams would need to re-shoot his scenes so that the anticipated spin-off could still meet its 2018 release date.

Unfortunately, Williams had committed himself to another project in Africa that was filming during the same time period: The Red Sea Diving Resort, an Argo-esque historical thriller from Homeland mastermind Gideon Raff. Based on a recently declassified F.B.I. operation, the film centers on spies smuggling persecuted Jews out of Ethiopia in the late 70s and early 80s through an abandoned resort they co-opted as a front for the operation. When a German travel agent started sending visitors to the resort, F.B.I. agents doubled as resort staff to maintain their cover.

By Max Montgomery.

“I would have had to be in London right now reshooting,” Williams says of Star Wars. “The only option was to cut my character from the film. But I feel very confident that I’ll be back in the galaxy, just not in the Han Solo project.”

Hearing Williams’s description of the character, we hope so: “He wore this beautiful white kimono, was very regal. He had class, money strength, charisma . . . and he knew how to fight. He was a warrior. He had a lot of prestige. If he lived in our world he would probably hang out with Jay Z and Beyoncé.”

“With the timing—I don't believe in mistakes,” Williams continues. “I believe I’m exactly where I’m supposed to be, and if it was meant to be, I would have been there.”

Traveling through Africa while filming The Red Sea Diving Resort has already afforded Williams one perk that a closed set in London could not: “Young people, they compliment me,” Williams says, astonished. “The Wire is airing in South Africa right now, and it’s very humbling. . . . I go to the hood in Kalecha, and they walk up and stop me and say, ‘Are you really here?'”

The experience reminds Williams of the way he connected to the characters in those classic, gritty 90s films. “It makes me feel like maybe I’m doing what people who walked before me did . . . Hopefully what Pac did for me, I get to do for somebody.”

Next month, Williams returns to the states for the Emmys. But the actor says he has learned to look for life’s awards outside of Hollywood ceremonies.

As he puts it: “The arts gave me something that no amount of money, no statue could—a life, a voice, a purpose.”

His mother, who invited herself as his date, doesn’t seem to mind the red-carpet detour though.

As for what his mom thought of his performance in The Night Of, Williams laughs.

“She was more of a Chalky White kind of gal. My family acknowledges what I’m doing but it kind of stops there. I’m not praised or singled out for what I do. We all have jobs in the Williams household.”

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The Big Orange Couch, Nickelodeon

For a generation of viewers, nothing said “stay up past your bedtime” like the inviting orange sofa that served as SNICK’s official mascot.

Courtesy of Nickelodeon.

The Couch at Central Perk, Friends

Really, those orange cushions were the seventh friend. (Sorry, Gunther.)

From Everett Collection.

The Simpson Family’s Couch, The Simpsons

The opening credits have transformed it into a giant whack-a-mole game, an electric chair, and a roller coaster, among countless other objects—but at heart, the Simpson family’s couch will always be the center of their all-American home.

From 20th Century Fox/Everett Collection.

D’Angelo Barksdale’s Orange Sofa, The Wire

Another orange couch—but this one is outside! And also a perfect meeting spot for Baltimore’s drug dealers.